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Iodotrimethylsilane

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Products Intro: Product Name:Iodotrimethylsilane
CAS:16029-98-4
Purity:0.99
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CAS:16029-98-4
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Products Intro: Product Name:Trimethylsilyl iodide(TMSI)
CAS:16029-98-4
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Products Intro: Product Name:Iodotrimethylsilane
CAS:16029-98-4
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Products Intro: Product Name:iodotrimethylsilane
CAS:16029-98-4
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  • Purity: 99%
  • Supply Ability: 50 tons
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Iodotrimethylsilane Basic information
Description Uses Preparation
Product Name:Iodotrimethylsilane
Synonyms:IODOTRIMETHYLSILANE;IODOTRIMETHYLSILYL IODIDE;TMIS;CT3610;iodotrimethyl-silan;Silane, iodotrimethyl-;trimethyliodosilane(tmis);TRIMETHYLIODOSILANE
CAS:16029-98-4
MF:C3H9ISi
MW:200.09
EINECS:240-171-0
Product Categories:Fine organic silicon;Alkyl Silanes;Si (Classes of Silicon Compounds);Blocking Agents;Protective Agents;Silylating Agents;Silane compounds;Silicon Compounds (for Synthesis);Si-X (F, Br, I) Compounds;Synthetic Organic Chemistry
Mol File:16029-98-4.mol
Iodotrimethylsilane Structure
Iodotrimethylsilane Chemical Properties
Melting point <0°C
Boiling point 106 °C(lit.)
density 1.406 g/mL at 25 °C(lit.)
refractive index n20/D 1.471(lit.)
Fp −25 °F
storage temp. -20°C
solubility reacts
form Liquid
color Clear colorless to reddish
Specific Gravity1.47
Water Solubility reacts
Sensitive Moisture & Light Sensitive
Hydrolytic Sensitivity8: reacts rapidly with moisture, water, protic solvents
BRN 1731136
InChIKeyCSRZQMIRAZTJOY-UHFFFAOYSA-N
CAS DataBase Reference16029-98-4(CAS DataBase Reference)
NIST Chemistry ReferenceIodotrimethylsilane(16029-98-4)
EPA Substance Registry SystemSilane, iodotrimethyl- (16029-98-4)
Safety Information
Hazard Codes F,C
Risk Statements 11-14-34
Safety Statements 16-26-36/37/39-43-45-25
RIDADR UN 2924 3/PG 2
WGK Germany 3
8-21
TSCA Yes
HazardClass 3
PackingGroup II
HS Code 29310095
MSDS Information
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Iodotrimethylsilane English
SigmaAldrich English
ACROS English
ALFA English
Iodotrimethylsilane Usage And Synthesis
DescriptionIodotrimethylsilane which has a hard acid (Me3Si) -soft base (I) bond displays a strong oxygenophilicity towards ethers, esters, lactones, acetals, and other molecules involving oxygen atom as a functional group.
The use of iodotrimethylsilane as the agent brought about a facile cleavage of the tert-butyl ester, giving the corresponding carboxylic acid in excellent yield.
Iodotrimethylsilane is used for the introduction of trimethylsilyl group in organic synthesis. It is also useful for gas chromatography analysis by converting alcohol into a silyl ether derivative, thereby making it more volatile than the original molecule.
Efficient reagent for cleaving ethers, esters, carbamates, ketals, and lactones.
For the introduction of the TMS group, e.g., TMS enol ethers.
Key reagent for the selective deprotection of an N-Cbz group in the presence of a trimethyltin moiety.
Reagent was recently reported to convert allyl- and benzylphosphotriesters to the corresponding iodides.
UsesTrimethylsilyliodide is a typical blocking agent in pharmaceutical manufacturing, widely used in the syntheses of drugs. It can protect or deprotect functional groups selectively, act as silane blocking agent.
PreparationIodotrimethylsilane, prepared by mixing equimolar amounts of chlorotrimethylsilane and sodium iodide in acetonitrile, reduces various benzylic alcohols to the corresponding phenylalkanes.
Iodotrimethylsilane is a multipurpose reagent used in various organic reactions. It is used for the dealkylation of few compounds like lactones, ethers, acetals, and carbamates and trimethylsilylating agent for the synthesis of silyl imino esters, alkyl and alkenyl silanes, etc. It also acts as a Lewis acid catalyst and as a reducing agent in many organic reactions.
Chemical PropertiesStraw liquid
Physical propertiesbp 106–109 °C; d 1.406 g cm?3; nD 20 1.4710; fp ?31 °C.
UsesIodotrimethylsilane can be used as a versatile reagent for the mild dealkylation of ethers, carboxylic esters, lactones, carbamates, acetals, phosphonate and phosphate esters; cleavage of epoxides, cyclopropyl ketones; conversion of vinyl phosphates to vinyl iodides; neutral nucleophilic reagent for halogen exchange reactions, carbonyl and conjugate addition reactions; use as a trimethylsilylating agent for formation of enol ethers, silyl imino esters, and N-silylenamines, alkyl, alkenyl and alkynyl silanes; Lewis acid catalyst for acetal formation, α- alkoxymethylation of ketones, for reactions of acetals with silyl enol ethers and allylsilanes; reducing agent for epoxides, enediones, α-ketols, sulfoxides, and sulfonyl halides; dehydrating agent for oximes.
UsesIodotrimethylsilane is an efficient reagent for ether, ester, carbamate, ketal, and lactone cleavage.
Preparationalthough more than 20 methods have been reported1 for the preparation of TMS-I, only a few are summarized here. chlorotrimethylsilane undergoes halogen exchange with either lithium iodide in CHCl3 or sodium iodide in MeCN, which allows in situ reagent formation. Alternatively, hexamethyldisilane reacts with iodine at 25–61°Cto afford TMS-I with no byproducts.

ReactionsTrimethylsilyl iodide reacts under mild conditions in the absence of a catalyst with alkyl fluorides as well as with benzyl and tertiary alkyl chlorides and bromides to give good yields of alkyl iodides and the corresponding trimethylsilyl halides.
Chemical SynthesisA 250-ml., two-necked, round-bottomed flask equipped with a magnetic stirring bar, an addition funnel for solids, and a reflux condenser bearing a nitrogen inlet is charged with 5.6 g. (0.21 mole) of aluminum powder and 16.2 g. (0.100 mole) of hexamethyldisiloxane and purged with nitrogen. The mixture is stirred and heated with an oil bath at 60° as 50.8 g. (0.200 mole) of iodine is added slowly through the addition funnel over 55 minutes. The bath temperature is raised to ca. 140°, and the mixture is heated under reflux for 1.5 hours. The reflux condenser is removed, and the flask is equipped for distillation at atmospheric pressure. The bath temperature is gradually raised from 140° to 210°, and the clear, colorless distillate is collected, yielding 32.6–35.3 g. (82–88%) of iodotrimethylsilane, b.p. 106–109°.
Purification MethodsAdd a little antimony powder and fractionate with this powder in the still. 20 1.470. Stabilise the distillate with 1% wt of Cu powder. [Eaborn J Chem Soc 3077 1950, Beilstein 4 IV 4009.]
Tag:Iodotrimethylsilane(16029-98-4) Related Product Information
Azidotrimethylsilane Trimethylsilyl cyanide N-(Trimethylsilyl)imidazole PROTEOGEL IPG STRIP 11 CM PH 6-11 PROTEOGEL IPG STRIP 11 CM PH 4-7 PROTEOGEL IPG STRIP 7 CM PH 6-11 PROTEOGEL IPG STRIP 18 CM PH 3-5 PROTEOGEL IPG STRIP 11 CM PH 3-5 PROTEOGEL IPG STRIP 11 CM PH 3-10 PROTEOGEL IPG STRIP 11 CM PH 8-11 PROTEOGEL IPG STRIP 18 CM PH 6-11 PROTEOGEL IPG STRIP 11 CM PH 5-8 PROTEOGEL IPG STRIP 7 CM PH 3-10 PROTEOGEL IPG STRIP 7 CM PH 3-5 triethyliodosilane N-(Trimethylsilyl)acetamide Iodotrimethylsilane tert-Butyldimethylsilyl chloride